p-Toluenesulfonic acid → HCID 86601657, 화합물

HRID 503679노트

반응식

HRID 503679 반응식
[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:32][CH2:33][O:34][S:35]([CH3:38])(=[O:37])=[O:36])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[C:21]([NH:23][CH2:24][CH:25]1[CH2:29][O:28]C(C)(C)[O:26]1)=[O:22])(=[O:4])=[O:3].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:38][S:35]([O:34][CH2:33][CH2:32][N:8]([CH2:7][CH2:6][O:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[C:21]([NH:23][CH2:24][CH:25]([OH:26])[CH2:29][OH:28])=[O:22])(=[O:36])=[O:37]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 118014282-(2-({[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]amino}carbonyl){2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate

생성물 1

HCID 86601657HCID 86601657, 화합물수율 73.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 2-(2-({[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]amino}carbonyl){2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate (13g) [Palmer et al., J. Med. Chem. 1997, 40, 1272] (5.0 mmol) in MeOH (200 mL) was treated with p-toluenesulfonic acid (0.2 g) at room temperature for 4 h. Most of the MeOH was then evaporated, and the residue was taken up in EtOAc (200 mL), washed with satd. NaHCO3 and brine, dried and concentrated. Chromatography of the product on silica gel, eluting with EtOAc/MeOH (20:1), gave 2-(2-{[(2,3-dihydroxypropyl)amino]carbonyl}{2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate (13f) (2.0 g, 73%): as yellow foam;

후처리

  1. customMost of the MeOH was then evaporated
  2. washwashed with satd
  3. dry with materialNaHCO3 and brine, dried
  4. concentrationconcentrated
  5. washChromatography of the product on silica gel, eluting with EtOAc/MeOH (20:1)

출처 및 근거

ORD 기록
ord-5e2489af56df4112bfc9efe5111f8a7f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776924B2

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